N-Phenyl-succinamic acid.

In the crystal structure of the title compound, C(10)H(11)NO(3), the conformations of N-H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are in syn positions with respect to each other. In the crystal, the mol-ecules are packed into infinite chains along the a axis through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures of anilides, see: Gowda et al. (2009 ▶, 2010 ▶). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For the packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C10H11NO3

M = 193.20

Monoclinic,

a = 4.986 (1) Å

b = 25.108 (4) Å

c = 7.895 (2) Å

β = 103.18 (2)°

V = 962.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.44 × 0.14 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.958, T max = 0.986

3269 measured reflections

1791 independent reflections

1033 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.135

S = 0.99

1791 reflections

133 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005364X/bq2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005364X/bq2265Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H11NO3	F(000) = 408
Mr = 193.20	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 702 reflections
a = 4.986 (1) Å	θ = 3.1–27.7°
b = 25.108 (4) Å	µ = 0.10 mm−1
c = 7.895 (2) Å	T = 293 K
β = 103.18 (2)°	Prism, colorless
V = 962.3 (3) Å3	0.44 × 0.14 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1791 independent reflections
Radiation source: fine-focus sealed tube	1033 reflections with I > 2σ(I)
graphite	Rint = 0.022
Rotation method data acquisition using ω scans	θmax = 25.7°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→6
Tmin = 0.958, Tmax = 0.986	k = −30→22
3269 measured reflections	l = −7→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3
1791 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.15 e Å−3
2 restraints	Δρmin = −0.13 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.3834 (4)	0.31826 (10)	0.9635 (3)	0.0421 (6)
C2	0.1411 (5)	0.33972 (11)	0.8656 (3)	0.0543 (7)
H2	0.0058	0.3177	0.8010	0.065*
C3	0.1030 (6)	0.39415 (12)	0.8651 (4)	0.0649 (8)
H3	−0.0589	0.4086	0.7989	0.078*
C4	0.2995 (6)	0.42738 (12)	0.9604 (4)	0.0702 (9)
H4	0.2712	0.4640	0.9589	0.084*
C5	0.5378 (6)	0.40589 (12)	1.0577 (4)	0.0697 (9)
H5	0.6720	0.4280	1.1229	0.084*
C6	0.5793 (5)	0.35204 (11)	1.0595 (3)	0.0562 (7)
H6	0.7418	0.3379	1.1263	0.067*
C7	0.2674 (5)	0.22230 (10)	0.9613 (3)	0.0448 (6)
C8	0.4033 (4)	0.16836 (10)	0.9852 (3)	0.0484 (7)
H8A	0.5575	0.1683	0.9293	0.058*
H8B	0.4757	0.1622	1.1085	0.058*
C9	0.2123 (4)	0.12352 (9)	0.9121 (3)	0.0504 (7)
H9A	0.0499	0.1255	0.9601	0.060*
H9B	0.1531	0.1280	0.7871	0.060*
C10	0.3391 (5)	0.06985 (10)	0.9496 (3)	0.0491 (7)
N1	0.4434 (4)	0.26322 (8)	0.9654 (3)	0.0483 (6)
H1N	0.616 (3)	0.2572 (10)	0.983 (3)	0.058*
O1	0.0199 (3)	0.22839 (7)	0.9463 (3)	0.0677 (6)
O2	0.5739 (3)	0.06282 (7)	1.0309 (3)	0.0701 (6)
O3	0.1737 (4)	0.03061 (7)	0.8868 (3)	0.0728 (7)
H3O	0.262 (5)	0.0004 (8)	0.913 (4)	0.087*

	U11	U22	U33	U12	U13	U23
C1	0.0303 (11)	0.0465 (16)	0.0499 (15)	0.0021 (11)	0.0102 (10)	0.0057 (12)
C2	0.0405 (14)	0.0548 (18)	0.0616 (17)	0.0040 (12)	−0.0005 (12)	0.0061 (14)
C3	0.0508 (16)	0.063 (2)	0.077 (2)	0.0145 (15)	0.0075 (14)	0.0158 (17)
C4	0.070 (2)	0.0465 (18)	0.097 (2)	0.0067 (16)	0.0269 (17)	0.0088 (17)
C5	0.0595 (19)	0.052 (2)	0.094 (2)	−0.0094 (15)	0.0099 (16)	−0.0023 (17)
C6	0.0377 (13)	0.0542 (18)	0.072 (2)	−0.0007 (13)	0.0018 (12)	0.0006 (14)
C7	0.0301 (13)	0.0461 (16)	0.0578 (16)	0.0006 (11)	0.0089 (10)	−0.0025 (12)
C8	0.0288 (12)	0.0505 (16)	0.0640 (17)	0.0025 (11)	0.0064 (11)	−0.0015 (13)
C9	0.0330 (12)	0.0470 (16)	0.0667 (17)	0.0044 (11)	0.0020 (11)	0.0003 (13)
C10	0.0344 (14)	0.0473 (16)	0.0619 (17)	−0.0001 (12)	0.0037 (12)	0.0007 (13)
N1	0.0241 (10)	0.0463 (14)	0.0721 (15)	0.0022 (10)	0.0057 (10)	0.0010 (11)
O1	0.0252 (9)	0.0548 (12)	0.1239 (17)	0.0050 (8)	0.0184 (9)	0.0050 (11)
O2	0.0411 (10)	0.0472 (11)	0.1055 (16)	0.0068 (8)	−0.0175 (10)	−0.0023 (10)
O3	0.0426 (10)	0.0436 (11)	0.1161 (17)	−0.0035 (9)	−0.0156 (10)	0.0047 (11)

C1—C6	1.382 (3)	C7—N1	1.347 (3)
C1—C2	1.386 (3)	C7—C8	1.507 (3)
C1—N1	1.413 (3)	C8—C9	1.503 (3)
C2—C3	1.380 (4)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.373 (4)	C9—C10	1.489 (3)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.370 (4)	C9—H9B	0.9700
C4—H4	0.9300	C10—O2	1.213 (3)
C5—C6	1.367 (4)	C10—O3	1.308 (3)
C5—H5	0.9300	N1—H1N	0.852 (16)
C6—H6	0.9300	O3—H3O	0.877 (17)
C7—O1	1.222 (3)
C6—C1—C2	119.0 (2)	N1—C7—C8	114.25 (19)
C6—C1—N1	118.2 (2)	C9—C8—C7	113.43 (18)
C2—C1—N1	122.8 (2)	C9—C8—H8A	108.9
C3—C2—C1	119.2 (2)	C7—C8—H8A	108.9
C3—C2—H2	120.4	C9—C8—H8B	108.9
C1—C2—H2	120.4	C7—C8—H8B	108.9
C4—C3—C2	121.3 (3)	H8A—C8—H8B	107.7
C4—C3—H3	119.3	C10—C9—C8	113.48 (19)
C2—C3—H3	119.3	C10—C9—H9A	108.9
C5—C4—C3	119.1 (3)	C8—C9—H9A	108.9
C5—C4—H4	120.4	C10—C9—H9B	108.9
C3—C4—H4	120.4	C8—C9—H9B	108.9
C6—C5—C4	120.4 (3)	H9A—C9—H9B	107.7
C6—C5—H5	119.8	O2—C10—O3	122.7 (2)
C4—C5—H5	119.8	O2—C10—C9	123.5 (2)
C5—C6—C1	121.0 (2)	O3—C10—C9	113.83 (19)
C5—C6—H6	119.5	C7—N1—C1	127.64 (19)
C1—C6—H6	119.5	C7—N1—H1N	119.7 (18)
O1—C7—N1	123.0 (2)	C1—N1—H1N	112.3 (18)
O1—C7—C8	122.7 (2)	C10—O3—H3O	108.8 (19)
C6—C1—C2—C3	0.7 (4)	N1—C7—C8—C9	−157.0 (2)
N1—C1—C2—C3	−177.3 (2)	C7—C8—C9—C10	−174.8 (2)
C1—C2—C3—C4	−0.4 (5)	C8—C9—C10—O2	−0.1 (4)
C2—C3—C4—C5	0.0 (5)	C8—C9—C10—O3	179.8 (2)
C3—C4—C5—C6	0.1 (5)	O1—C7—N1—C1	3.7 (4)
C4—C5—C6—C1	0.1 (4)	C8—C7—N1—C1	−173.5 (2)
C2—C1—C6—C5	−0.5 (4)	C6—C1—N1—C7	144.5 (3)
N1—C1—C6—C5	177.5 (2)	C2—C1—N1—C7	−37.5 (4)
O1—C7—C8—C9	25.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.22 (2)	3.041 (3)	161 (2)
O3—H3O···O2ii	0.88 (2)	1.80 (2)	2.671 (2)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.22 (2)	3.041 (3)	161 (2)
O3—H3O⋯O2ii	0.88 (2)	1.80 (2)	2.671 (2)	177 (3)

Symmetry codes: (i) ; (ii) .